Aluminium lithium hydride → HCID 11447712, compound

HRID 965879Notes

Reaction equation

HRID 965879 reaction equation
C(OC(=O)[C:5]([NH:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([C:14]2[CH2:23][CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=2)[CH:9]=1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:22][CH2:23][C:14]=1[C:10]1[CH:9]=[C:8]([NH:7][CH3:5])[CH:13]=[CH:12][N:11]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 69592134HCID 69592134, compound

Product 1

HCID 11447712HCID 11447712, compoundYield 42.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of N-[2-(3,4-dihydro-naphthalen-2-yl)-pyridin-4-yl]-oxalamic acid ethyl ester (0.36 g, 1.2 mmol) in THF (20 ml) was slowly added to an ice bath cooled mixture of lithium aluminum hydride (0.10 g , 2.6 mmol) in THF (20 ml). The resulting mixture was refluxed for 30 min, quenched with aqueous saturated Seignette-salt solution and extracted with AcOEt. The organic phase was dried over Na2SO4, concentrated and chromatographed (SiO2 with CH2Cl2/CH3OH/NH4OH=140/10/1) to give [2-(3,4-dihydro-naphthalen-2-yl)-pyridin-4-yl]-methyl-amine as a yellow oil (0.12 g, 42%) which was crystallized as the white fumarate salt. Mp. 106-107° C. (MeOH/Et2O), MS: m/e=236 (M+).

Workup

  1. temperaturecooled
  2. temperatureThe resulting mixture was refluxed for 30 min
  3. customquenched with aqueous saturated Seignette-salt solution
  4. extractionextracted with AcOEt
  5. dry with materialThe organic phase was dried over Na2SO4
  6. concentrationconcentrated
  7. customchromatographed (SiO2 with CH2Cl2/CH3OH/NH4OH=140/10/1)

Sources & evidence

ORD record
ord-c4e7b5af35d94d36b4cac0f87133df68
Source dataset
uspto-grants-2005_10
Patent number
US06951875B2

Reaction notes

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